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Cheap flights from Chicago Midway Airport to Milan from $350

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago Midway Airport to Milan departing on 6/11. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
1 adult, Economy, 0 bags

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Find the cheapest flights from Chicago Midway Airport to Milan

Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
7:30 am - 7:00 am
MDW
-
MXP
16h 30m
1 stop
Multiple Airlines Logo
11:25 pm - 9:45 am
MXP
-
MDW
41h 20m
2 stops
$886Multiple Airlines
Mon, Apr 20 - Tue, May 5
Multiple Airlines Logo
6:40 am - 11:00 am
MDW
-
MXP
21h 20m
2 stops
Multiple Airlines Logo
6:55 am - 10:00 pm
MXP
-
MDW
22h 05m
2 stops
$927Multiple Airlines
Tue, Sep 1 - Thu, Sep 10
Multiple Airlines Logo
7:40 am - 9:20 pm
MDW
-
MXP
30h 40m
2 stops
Multiple Airlines Logo
6:55 am - 6:35 pm
MXP
-
MDW
18h 40m
2 stops
$1,023Multiple Airlines
Mon, Jun 8 - Thu, Jun 18
Multiple Airlines Logo
5:15 am - 3:50 pm
MDW
-
MXP
27h 35m
2 stops
Multiple Airlines Logo
7:00 am - 7:20 pm
MXP
-
MDW
19h 20m
2 stops
$1,033Multiple Airlines
Sun, Jun 7 - Wed, Jun 10
Multiple Airlines Logo
10:25 am - 12:40 am
MDW
-
MXP
31h 15m
3 stops
Multiple Airlines Logo
6:40 am - 2:35 pm
MXP
-
MDW
38h 55m
3 stops
$1,037Multiple Airlines
Thu, Jun 11 - Mon, Jun 22
Multiple Airlines Logo
7:30 am - 7:00 am
MDW
-
MXP
16h 30m
1 stop
Multiple Airlines Logo
11:50 am - 1:00 pm
MXP
-
MDW
32h 10m
2 stops
$1,039Multiple Airlines
Sat, Apr 25 - Fri, May 1
Delta Logo
1:00 pm - 11:20 am
MDW
-
LIN
15h 20m
2 stops
Delta Logo
6:30 am - 4:22 pm
LIN
-
MDW
16h 52m
2 stops
$1,324Delta
Sat, Aug 22 - Wed, Dec 23
Delta Logo
1:00 pm - 10:05 am
MDW
-
LIN
14h 05m
2 stops
Delta Logo
6:40 am - 6:31 pm
LIN
-
MDW
18h 51m
2 stops
$1,527Delta
Fri, Aug 28 - Sun, Sep 13
Delta Logo
11:05 am - 8:50 am
MDW
-
LIN
14h 45m
2 stops
Delta Logo
6:40 am - 6:31 pm
LIN
-
MDW
18h 51m
2 stops
$1,618Delta
Wed, Jun 24 - Wed, Jul 1
KLM Logo
6:36 pm - 3:55 pm
MDW
-
LIN
14h 19m
2 stops
KLM Logo
11:00 am - 6:33 pm
LIN
-
MDW
14h 33m
2 stops
$1,728KLM
Sun, May 10 - Tue, May 26

Delta flights from Chicago Midway Airport to Milan

Our best Delta deals on Chicago Midway Airport to Milan flight tickets
Delta
Aug 22
MDW9:30 amChicago Midway
18h 10m
2 stops
MXP10:40 amMilan Malpensa
Aug 30
MXP11:40 amMilan Malpensa
17h 06m
1 stop
MDW9:46 pmChicago Midway
$1,310
Delta
Aug 22
MDW9:30 amChicago Midway
18h 10m
2 stops
MXP10:40 amMilan Malpensa
Aug 30
MXP9:00 amMilan Malpensa
19h 46m
2 stops
MDW9:46 pmChicago Midway
$1,314
Delta
Aug 22
MDW1:00 pmChicago Midway
14h 40m
2 stops
MXP10:40 amMilan Malpensa
Dec 23
MXP6:55 amMilan Malpensa
16h 27m
2 stops
MDW4:22 pmChicago Midway
$1,320

KLM flights from Chicago Midway Airport to Milan

Our best KLM deals on Chicago Midway Airport to Milan flight tickets
KLM
Sep 27
MDW1:05 pmChicago Midway
13h 20m
1 stop
MXP9:25 amMilan Malpensa
Oct 8
MXP11:40 amMilan Malpensa
17h 05m
1 stop
MDW9:45 pmChicago Midway
$1,341
KLM
Apr 23
MDW12:52 pmChicago Midway
13h 33m
1 stop
MXP9:25 amMilan Malpensa
May 8
MXP11:40 amMilan Malpensa
16h 46m
1 stop
MDW9:26 pmChicago Midway
$1,701
KLM
May 10
MDW6:36 pmChicago Midway
14h 19m
2 stops
LIN3:55 pmMilan Linate
May 26
LIN11:00 amMilan Linate
14h 33m
2 stops
MDW6:33 pmChicago Midway
$1,728

momondo Fare Finder

 
Customize your flight search to find flights from Chicago Midway Airport to Milan that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated April 10, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Milan that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Mon 4/20

7:30 am-7:00 am

1 stop16h 30m

Milan Malpensa

Tue 5/5

11:25 pm-9:45 am

2 stops41h 20m

$886

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Tue 9/1

6:40 am-11:00 am

2 stops21h 20m

Milan Malpensa

Thu 9/10

6:55 am-10:00 pm

2 stops22h 05m

$927

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Mon 6/8

7:40 am-9:20 pm

2 stops30h 40m

Milan Malpensa

Thu 6/18

6:55 am-6:35 pm

2 stops18h 40m

$1,023

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Sun 6/7

5:15 am-3:50 pm

2 stops27h 35m

Milan Malpensa

Wed 6/10

7:00 am-7:20 pm

2 stops19h 20m

$1,033

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Thu 6/11

10:25 am-12:40 am

3 stops31h 15m

Milan Malpensa

Mon 6/22

6:40 am-2:35 pm

3 stops38h 55m

$1,037

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Sat 4/25

7:30 am-7:00 am

1 stop16h 30m

Milan Malpensa

Fri 5/1

11:50 am-1:00 pm

2 stops32h 10m

$1,039

ChicagoMilan

MDW - LIN

MDWLIN

Chicago Midway

Sat 8/22

1:00 pm-11:20 am

2 stops15h 20m

Milan Linate

Wed 12/23

6:30 am-4:22 pm

2 stops16h 52m

$1,324

ChicagoMilan

MDW - LIN

MDWLIN

Chicago Midway

Fri 8/28

1:00 pm-10:05 am

2 stops14h 05m

Milan Linate

Sun 9/13

6:40 am-6:31 pm

2 stops18h 51m

$1,527

ChicagoMilan

MDW - LIN

MDWLIN

Chicago Midway

Wed 6/24

11:05 am-8:50 am

2 stops14h 45m

Milan Linate

Wed 7/1

6:40 am-6:31 pm

2 stops18h 51m

$1,618
Quickest round-trip

ChicagoMilan

MDW - LIN

MDWLIN

Chicago Midway

Sun 5/10

6:36 pm-3:55 pm

2 stops14h 19m

Milan Linate

Tue 5/26

11:00 am-6:33 pm

2 stops14h 33m

$1,728

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Milan from

How to get the cheapest flight ticket from Chicago Midway Airport to Milan

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest day to depart on your flight to Milan?

Our data shows that Tuesday is the least expensive day to fly to Milan. Tickets to fly out on this day can be as low as $1,213. The most expensive day to fly to Milan is Thursday, with ticket prices averaging around $1,361.

Can stopping save me money on Chicago Midway Airport to Milan flights?

You could potentially save up to 2% on your flight if you consider stops on a Chicago Midway Airport to Milan flight.

When to book flights from Chicago Midway Airport to Milan

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago Midway Airport to Milan according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Chicago Midway Airport to Milan (MDW to MIL) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago Midway Airport to Milan

Fastest flight time

11h 45m

Direct flights

None
The fastest flight from Chicago Midway Airport to Milan takes 11h 45m
There are no direct flights from Chicago Midway Airport to Milan. There are no popular flight routes from Chicago Midway Airport to Milan.
Search flight deals

Frequently asked questions about flying from Chicago Midway Airport to Milan

  • How far is Chicago Midway to Milan by plane?

    Milan is 4534.8 mi away from Chicago Midway. Flights usually cover this in 11h 45m, depending on flying conditions and air traffic around both airports.

  • When did momondo last update prices for flights from Chicago Midway Airport to Milan?

    Prices for flights from Chicago Midway Airport to Milan are updated daily.

  • How old do you have to be to fly from Chicago Midway Airport to Milan?

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago Midway Airport to Milan.

  • What documentation or ID do you need to fly to Milan?

    The necessary travel and health documents for your Milan trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

Traveling to a place near Milan?

Book flights to Milan if you plan to visit one of these locations
Bellagio
Varenna
Menaggio
Stresa
Brescia
Livigno
Levanto
Assago
Monza
Bellano
Lecco
Crema
Rho
Domodossola
Cernobbio
Moltrasio
Bormio
Novara
Baveno
Saronno

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Milan?

Finding the right flight to Milan from Chicago is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Milan quick and easy, saving you time and money.

Can I find flights from Chicago to Milan with flexible booking policies on momondo?

Yes. momondo enables you to select and highlight flights to Milan from Chicago with this policy.

How can momondo help me find flights from Chicago to Milan?

Once you have performed a search for Chicago to Milan flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

I’m not ready to book a flight from Chicago to Milan right now. Can momondo alert me if prices change?

If you are not ready to book a flight from Chicago to Milan now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Milan and let you know when they change.

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Find better results for your trip to Italy

Fly into one of these airports located in Milan

Airports listed have a maximum distance of 25.0 mi from Milan
Milan Linate Airport
Milan Malpensa Airport